Electrolyte‐controlled regiodivergent continuous flow electroselenocyclisations

Arepally, Sagar, Gieman, Hanaa and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 2025. Electrolyte‐controlled regiodivergent continuous flow electroselenocyclisations. Angewandte Chemie - International Edition 64 (38) , e202509811. 10.1002/anie.202509811

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Abstract

Supporting electrolytes, beyond traditionally serving as ionic conductors in electrochemistry, can influence regioselectivity in electrochemical synthesis by acting as base. We present a single‐pass continuous flow electrolysis method enabling selective activation of diselenides and oximes to access seleno‐substituted isoquinoline and isoindole derivatives. Mechanistic studies showed a radical pathway via iminoxyl radicals to isoindole N‐oxides and an ionic mechanism leading to isoquinoline N‐oxides. This process leverages N‐activated neutral isoquinolinium products for diverse downstream modifications. Our findings highlight the untapped potential of supporting electrolytes in regiodivergent electrochemical transformations and provide a sustainable and scalable platform for continuous flow approaches for synthesising selenium‐containing heterocycles with biological relevance.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry
Additional Information:	License information from Publisher: LICENSE 1: URL: http://creativecommons.org/licenses/by/4.0/ German translation in Angewandte Chemie, DOI: 10.1002/ange.202509811
Publisher:	Wiley-Blackwell
ISSN:	1433-7851
Date of First Compliant Deposit:	11 August 2025
Date of Acceptance:	22 July 2025
Last Modified:	01 Oct 2025 13:30
URI:	https://orca.cardiff.ac.uk/id/eprint/180352

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